53+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. New York
  3. Pine Plains

Pine Plains pickleball Stays, Resort Rentals, & Homes

About Pine Plains Vacation Rentals

Discover over 53 amazing vacation rental options in Pine Plains with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Pine Plains.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 2571.03 ft², with prices averaging US $717 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Pine Plains.

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Top Pickleball-Ready Accommodation Types in Pine Plains

Type Count
Vacation Homes 43
Holiday Apartments 3

Use these Quick Filters to Find a Vacation Rental in Pine Plains

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Pine Plains with PickleTrip™.

Weather in Pine Plains, NY

View the weather forecast for Pine Plains before booking your Pine Plains Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Pine Plains, NY

PickleTrip offers a large selection of top attractions around Pine Plains . Research things to do on your vacation before you visit Pine Plains.


Thompson Pond
Train Station
Ski Butternut
Catamount Ski Area
Mohawk Mountain Ski Area
Bard College
Kent Falls State Park
Omega Institute
Franklin D. Roosevelt Presidential Library and Museum
Dutchess County Fairgrounds
Lime Rock Park
Lake Waramaug State Park
Ulster Performing Arts Center
Saugerties Lighthouse
Millbrook Vineyards and Winery
Vanderbilt Mansion National Historic Site
Olana State Historic Site
Hudson Valley Mall
Home of Franklin D. Roosevelt National Historic Site
Forsyth Park

Other Places to Stay in Pine Plains, NY


Thompson Pond 29 Properties

Frequently Asked Questions About Pine Plains?

What are the top vacation rentals, resorts, and hotels in Pine Plains with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Pine Plains. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Pine Plains!

Which vacation rentals, resorts, or hotels in Pine Plains is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Pine Plains? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Pine Plains?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 53 properties listed in Pine Plains in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.


People Also Ask

There are 53 Pine Plains, NY Vacation Rentals

Recently Booked Vacation Rentals in Pine Plains